Originally, the company's business model was based on selling advertising and sponsorship. Following the collapse of the Dot-com bubble in 2000, the company looked towards publishing as an alternative source of income.[4] The company's first book, Build Your Own Database Driven Website Using PHP and MySQL, was published that November, based on a popular online tutorial.[6] Originally made available using print on demand, the book went on to sell 20,000 copies.[4] By 2004, the company had published six books, and began distribution through O'Reilly.[7]

The SitePoint Marketplace, a spinoff from the site's existing forums, was launched in 2005 as a forum in which web designers and developers could outsource projects. In 2007, part of the marketplace was spun off as 99designs, an online marketplace for crowdsourced graphic design.[8] In 2011, 99designs received its first outside investment in the form of $35 million in venture capital funding from Accel Partners.[9]

Following the introduction of its own courses, the company launched Learnable in 2010 as a new online learning platform for web developers.[13] Originally designed as a marketplace, it is now the primary outlet for SitePoint's online book and course products.[14]